Identification

Name
Theophylline
Accession Number
DB00277  (APRD00082, DB09359)
Type
Small Molecule
Groups
Approved
Description

A methylxanthine derivative from tea with diuretic, smooth muscle relaxant, bronchial dilation, cardiac and central nervous system stimulant activities. Mechanistically, theophylline acts as a phosphodiesterase inhibitor, adenosine receptor blocker, and histone deacetylase activator. Theophylline is marketed under several brand names such as Uniphyl and Theochron, and it is indicated mainly for asthma, bronchospasm, and COPD.

Structure
Thumb
Synonyms
  • 1,3-dimethyl-7H-purine-2,6-dione
  • 1,3-dimethylxanthine
  • Teofilina
  • Theophyllin
  • Theophylline anhydrous
  • Theophylline, anhydrous
Product Ingredients
IngredientUNIICASInChI Key
Theophylline sodium glycinate2S36N8T7538000-10-0AIJQWRAOMFRHTQ-UHFFFAOYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Elixir De TheophyllineElixir80 mgOralLaboratoire Atlas Inc1985-12-31Not applicableCanada
ElixophyllineLiquid80 mg/15mLOralFOREST PHARMACEUTICALS, INC.2006-10-16Not applicableUs
Pulmophylline ElxElixir80 mgOralLaboratoire Riva Inc1979-12-31Not applicableCanada
Quibron T SR Tab 300mgTablet, extended release300 mgOralBristol Labs Division Of Bristol Myers Squibb1982-12-312004-08-05Canada
Quibron-TTablet300 mg/1OralMonarch Pharmaceuticals, Inc.2006-11-09Not applicableUs
Slo-bid 100Capsule, extended release100 mgOralAventis Pharma Ltd.1987-12-312003-07-22Canada
Slo-bid 200Capsule, extended release200 mgOralAventis Pharma Ltd.1987-12-312003-07-22Canada
Slo-bid 300Capsule, extended release300 mgOralAventis Pharma Ltd.1987-12-312002-07-29Canada
Slo-bid 50Capsule, extended release50 mgOralAventis Pharma Ltd.1988-12-312003-07-22Canada
Theo ERTablet, extended release400 mgOralAa Pharma Inc2011-06-23Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-theo ERTablet, extended release600 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-theo ERTablet, extended release400 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-theo-LA Srt 100mgTablet, extended release100 mgOralApotex Corporation1993-12-31Not applicableCanada
Apo-theo-LA Srt 200mgTablet, extended release200 mgOralApotex Corporation1993-12-31Not applicableCanada
Apo-theo-LA Srt 300mgTablet, extended release300 mgOralApotex Corporation1993-12-31Not applicableCanada
ElixophyllinLiquid80 mg/15mLOralCaraco Pharma, Inc.2009-10-01Not applicableUs
ElixophyllinLiquid80 mg/15mLOralNostrum Laboratories, Inc.2009-10-01Not applicableUs
ElixophyllinLiquid80 mg/15mLOralAtlantic Biologicals Corps.2009-10-01Not applicableUs
ElixophyllinLiquid80 mg/15mLOralCarilion Materials Management2009-10-01Not applicableUs
PMS-theophylline ElixirElixir80 mgOralPharmascience Inc1983-12-312016-10-28Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
I D M Expectorant TabTheophylline (70 mg) + Guaifenesin (100 mg) + Mepyramine maleate (12 mg) + Potassium Iodide (160 mg)TabletOralRougier Pharma Division Of Ratiopharm Inc1975-12-311999-09-27Canada
Idm TabTheophylline (140 mg) + Mepyramine maleate (25 mg) + Potassium Iodide (325 mg)TabletOralRougier Pharma Division Of Ratiopharm Inc1977-12-311999-09-27Canada
Ratio-theo-broncTheophylline (7 mg) + Guaifenesin (10 mg) + Mepyramine maleate (1.2 mg) + Potassium Iodide (16 mg)SyrupOralRatiopharm Inc Division Of Teva Canada Limited1964-12-312015-10-26Canada
Tedral TabTheophylline (118 mg) + Ephedrine hydrochloride (24 mg) + Phenobarbital (8 mg)TabletOralParke Davis Division, Warner Lambert Canada Inc.1981-12-311999-08-13Canada
Theophylline 0.8mg and 5% Dextrose InjTheophylline (.8 mg) + Dextrose, unspecified form (50 mg)SolutionIntravenousBaxter Laboratories1989-12-312008-11-07Canada
Theophylline 0.8mg/ml In 5% Dextrose InjTheophylline (0.8 mg) + Dextrose, unspecified form (5.0 %)SolutionIntravenousHospira, Inc.1986-12-312011-08-05Canada
Theophylline 1.6mg and 5% Dextrose InjTheophylline (1.6 mg) + Dextrose, unspecified form (50 mg)SolutionIntravenousBaxter Laboratories1989-12-312008-11-07Canada
Theophylline 4mg and 5% Dextrose InjTheophylline (4 mg) + Dextrose, unspecified form (50 mg)SolutionIntravenousBaxter Laboratories1995-12-312005-07-29Canada
Theophylline in DextroseTheophylline (160 mg/100mL) + D-glucose monohydrate (5 g/100mL)InjectionIntravenousB. Braun Medical Inc.2008-01-082008-01-08Us
Theophylline in DextroseTheophylline (80 mg/100mL) + D-glucose monohydrate (5 g/100mL)Injection, solutionIntravenousB. Braun Medical Inc.1992-08-14Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
SenophyllineTheophylline (100 mg/1) + Choline (250 mg/1)KitPhysician Therapeutics Llc2011-07-07Not applicableUs
International/Other Brands
Quibron-T / Respbid / Slo-Bid / Theo 24 / Theo-Dur / Theodur G
Categories
UNII
0I55128JYK
CAS number
58-55-9
Weight
Average: 180.164
Monoisotopic: 180.06472552
Chemical Formula
C7H8N4O2
InChI Key
ZFXYFBGIUFBOJW-UHFFFAOYSA-N
InChI
InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
IUPAC Name
1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
CN1C2=C(NC=N2)C(=O)N(C)C1=O

Pharmacology

Indication

For the treatment of the symptoms and reversible airflow obstruction associated with chronic asthma and other chronic lung diseases, such as emphysema and chronic bronchitis.

Associated Conditions
Pharmacodynamics

Theophylline, an xanthine derivative chemically similar to caffeine and theobromine, is used to treat asthma and bronchospasm. Theophylline has two distinct actions in the airways of patients with reversible (asthmatic) obstruction; smooth muscle relaxation (i.e., bronchodilation) and suppression of the response of the airways to stimuli (i.e., non-bronchodilator prophylactic effects).

Mechanism of action

Theophylline relaxes the smooth muscle of the bronchial airways and pulmonary blood vessels and reduces airway responsiveness to histamine, methacholine, adenosine, and allergen. Theophylline competitively inhibits type III and type IV phosphodiesterase (PDE), the enzyme responsible for breaking down cyclic AMP in smooth muscle cells, possibly resulting in bronchodilation. Theophylline also binds to the adenosine A2B receptor and blocks adenosine mediated bronchoconstriction. In inflammatory states, theophylline activates histone deacetylase to prevent transcription of inflammatory genes that require the acetylation of histones for transcription to begin.

TargetActionsOrganism
AAdenosine receptor A1
antagonist
Human
AAdenosine receptor A2a
antagonist
Human
AAdenosine receptor A2b
antagonist
Human
AcAMP-specific 3',5'-cyclic phosphodiesterase 4B
inhibitor
Human
AcGMP-specific 3',5'-cyclic phosphodiesterase
inhibitor
Human
AcAMP-specific 3',5'-cyclic phosphodiesterase 4A
inhibitor
Human
AcGMP-inhibited 3',5'-cyclic phosphodiesterase A
inhibitor
Human
AHistone deacetylase 2
activator
Human
UCopine-1Not AvailableHuman
UMinor histocompatibility antigen H13Not AvailableHuman
UNodal modulator 1Not AvailableHuman
UPoly [ADP-ribose] polymerase 1Not AvailableHuman
UProtein RIC-3Not AvailableHuman
UTubulin monoglycylase TTLL3Not AvailableHuman
Absorption

Theophylline is rapidly and completely absorbed after oral administration in solution or immediate-release solid oral dosage form.

Volume of distribution
  • 0.3 to 0.7 L/kg
Protein binding

40%, primarily to albumin.

Metabolism

Hepatic. Biotransformation takes place through demethylation to 1-methylxanthine and 3-methylxanthine and hydroxylation to 1,3-dimethyluric acid. 1-methylxanthine is further hydroxylated, by xanthine oxidase, to 1-methyluric acid. About 6% of a theophylline dose is N-methylated to caffeine. Caffeine and 3-methylxanthine are the only theophylline metabolites with pharmacologic activity.

Route of elimination

Theophylline does not undergo any appreciable pre-systemic elimination, distributes freely into fat-free tissues and is extensively metabolized in the liver. Renal excretion of unchanged theophylline in neonates amounts to about 50% of the dose, compared to about 10% in children older than three months and in adults.

Half life

8 hours

Clearance
  • 0.29 mL/kg/min [Premature neonates, postnatal age 3-15 days]
  • 0.64 mL/kg/min [Premature neonates, postnatal age 25-57 days]
  • 1.7 mL/kg/min [Children 1-4 years]
  • 1.6 mL/kg/min [Children 4-12 years]
  • 0.9 mL/kg/min [Children 13-15 years]
  • 1.4 mL/kg/min [Children 16-17 years]
  • 0.65 mL/kg/min [Adults (16-60 years), otherwise healthy non-smoking asthmatics]
  • 0.41 mL/kg/min [Elderly (>60 years), non-smokers with normal cardiac, liver, and renal function]
  • 0.33 mL/kg/min [Acute pulmonary edema]
  • 0.54 mL/kg/min [COPD >60 years, stable, non-smoker >1 year]
  • 0.48 mL/kg/min [COPD with cor pulmonale]
  • 1.25 mL/kg/min [Cystic fibrosis (14-28 years)]
  • 0.31 mL/kg/min [Liver disease cirrhosis]
  • 0.35 mL/kg/min [acute hepatitis]
  • 0.65 mL/kg/min [cholestasis]
  • 0.47 mL/kg/min [Sepsis with multi-organ failure]
  • 0.38 mL/kg/min [hypothyroid]
  • 0.8 mL/kg/min [hyperthyroid]
Toxicity

Symptoms of overdose include seizures, arrhythmias, and GI effects.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Caffeine MetabolismMetabolic
Caffeine MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 1A2-2964(G/A)(A;A) / (G;A)A AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of theophylline.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of Theophylline can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of Theophylline can be decreased when combined with (S)-Warfarin.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Theophylline.
3,5-diiodothyropropionic acidThe metabolism of Theophylline can be decreased when combined with 3,5-diiodothyropropionic acid.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Theophylline.
4-MethoxyamphetamineThe metabolism of Theophylline can be decreased when combined with 4-Methoxyamphetamine.
5-androstenedioneThe metabolism of Theophylline can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Theophylline can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of Theophylline can be decreased when combined with 6-O-benzylguanine.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with Theophylline.
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Take with food.

References

Synthesis Reference

Nicolae S. Bodor, Kenneth B. Sloan, Yu-Neng Kuo, "Method for synthesizing certain selected pro-drug forms of theophylline." U.S. Patent US4000132, issued January, 1956.

US4000132
General References
Not Available
External Links
Human Metabolome Database
HMDB0001889
KEGG Drug
D00371
KEGG Compound
C07130
PubChem Compound
2153
PubChem Substance
46505949
ChemSpider
2068
BindingDB
10847
ChEBI
28177
ChEMBL
CHEMBL190
Therapeutic Targets Database
DAP000002
PharmGKB
PA451647
IUPHAR
413
Guide to Pharmacology
GtP Drug Page
HET
TEP
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Theophylline
ATC Codes
R03DA54 — Theophylline, combinations excl. psycholepticsR03DA74 — Theophylline, combinations with psycholepticsR03DA04 — TheophyllineR03DB04 — Theophylline and adrenergics
AHFS Codes
  • 86:16.00 — Respiratory Smooth Muscle Relaxants
PDB Entries
1eht / 1o15 / 2a3a / 3rox / 4eoh / 5mzj
FDA label
Download (85.2 KB)
MSDS
Download (75.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceMountain Sickness1
1CompletedBasic SciencePharmacokinetics2
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHigh Altitude Pulmonary Hypertension1
1CompletedTreatmentMajor Depressive Disorder (MDD)1
1CompletedTreatmentProstate Neoplasms1
1RecruitingTreatmentAdvanced Solid Malignancies / Lung Cancer Non-Small Cell Cancer (NSCLC)1
1WithdrawnTreatmentLung Cancer Non-Small Cell Cancer (NSCLC) / Lung Cancers1
1, 2CompletedPreventionPhysiological Function in Low Oxygen Environment1
1, 2CompletedTreatmentAcute Myelogenous Leukaemia (AML)1
2CompletedTreatmentAcute maxillary sinusitis caused by M. catarrhalis / Allergic Rhinitis (AR) / Asthma Bronchial1
2CompletedTreatmentAlbright Hereditary Osteodystrophy / Pseudohypoparathyroidism Type 1a1
2CompletedTreatmentLeukemias1
2RecruitingTreatmentAlbright Hereditary Osteodystrophy / Pseudohypoparathyroidism1
2RecruitingTreatmentEnd Stage Renal Disease (ESRD) / Olfactory Disorders1
2, 3CompletedNot AvailableOther and unspecified effects of high altitude1
2, 3CompletedTreatmentAsthma Bronchial1
2, 3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2, 3CompletedTreatmentPrimary apnea of premature newborns1
2, 3Unknown StatusPreventionProphylaxis of Contrast-induced nephropathy1
3CompletedSupportive CarePulmonary Complications / Quality of Life / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedTreatmentAsthma Bronchial2
3CompletedTreatmentAsthma Bronchial / Chronic Lung Diseases1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)2
4Active Not RecruitingTreatmentAsthma Bronchial1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedHealth Services ResearchAsthma Bronchial1
4CompletedPreventionAdverse Effects / Contrast Induced Nephropathy (CIN) / Kidney Diseases / Renal Failure1
4CompletedTreatmentAsthma Bronchial1
4CompletedTreatmentBronchiectasis2
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)2
4Not Yet RecruitingOtherPHP Ia / PHP IB / Php1C1
Not AvailableCompletedNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedTreatmentFunction of Renal Transplant1
Not AvailableRecruitingNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableRecruitingDevice FeasibilityHeart Ventricles1
Not AvailableUnknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1

Pharmacoeconomics

Manufacturers
  • Fleming and co pharmaceuticals inc
  • Forest laboratories inc
  • Sanofi aventis us llc
  • Dm graham laboratories inc
  • Ucb inc
  • Whitby pharmaceuticals inc
  • Schwarz pharma inc
  • Schering corp
  • Central pharmaceuticals inc
  • Hospira inc
  • Inwood laboratories inc sub forest laboratories inc
  • Sandoz inc
  • Rp scherer north america div rp scherer corp
  • Ortho mcneil pharmaceutical inc
  • Schering corp sub schering plough corp
  • Fisons corp
  • Kv pharmaceutical co
  • Rp scherer north america
  • Hr cenci laboratories inc
  • Caraco pharmaceutical laboratories ltd
  • Lannett co inc
  • Panray corp sub ormont drug and chemical co inc
  • Alpharma us pharmaceuticals division
  • Cenci powder products inc
  • Halsey drug co inc
  • L perrigo co
  • Pharmaceutical assoc inc div beach products
  • Precision dose inc
  • Roxane laboratories inc
  • Taro pharmaceuticals usa inc
  • Wockhardt eu operations (swiss) ag
  • B braun medical inc
  • Baxter healthcare corp
  • 3m pharmaceuticals inc
  • Ferndale laboratories inc
  • Warner chilcott co llc
  • Monarch pharmaceuticals inc
  • Roerig div pfizer inc
  • Able laboratories inc
  • Glenmark generics ltd
  • Nostrum pharmaceuticals inc
  • Pliva inc
  • Pharmaceutical research assoc inc
  • Purdue pharmaceutical products lp
  • Graceway pharmaceuticals llc
  • Novartis consumer health inc
Packagers
  • Actavis Group
  • Amend
  • American Regent
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotheca Inc.
  • Arcola Laboratories
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • B. Braun Melsungen AG
  • BASF Corp.
  • Baxter International Inc.
  • Bristol-Myers Squibb Co.
  • C.O. Truxton Inc.
  • Cardinal Health
  • Caremark LLC
  • Central Texas Community Health Centers
  • Comprehensive Consultant Services Inc.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Emcure Pharmaceuticals Ltd.
  • Equipharm Inc.
  • Forest Laboratories Inc.
  • Forest Pharmaceuticals
  • Glenmark Generics Ltd.
  • H and H Laboratories
  • Heartland Repack Services LLC
  • Hospira Inc.
  • Inwood Labs
  • Inyx Usa Ltd.
  • Kaiser Foundation Hospital
  • Luitpold Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Marlop Pharmaceuticals Inc.
  • Mckesson Corp.
  • Mundipharma GmbH
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nostrum Laboratories Inc.
  • Nucare Pharmaceuticals Inc.
  • P F Laboratories Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Packaging Center
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Purdue Pharma LP
  • Qualitest
  • Remedy Repack
  • Rite Aid Corp.
  • Roxane Labs
  • Roxmar Laboratories
  • Sandhills Packaging Inc.
  • Sandoz
  • Sanofi-Aventis Inc.
  • Southwood Pharmaceuticals
  • Talbert Medical Management Corp.
  • Taro Pharmaceuticals USA
  • Tya Pharmaceuticals
  • UCB Pharma
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • Warrick Pharmaceuticals Corp.
  • Wockhardt Ltd.
Dosage forms
FormRouteStrength
Tablet, extended releaseOral100 mg
Tablet, extended releaseOral200 mg
Tablet, extended releaseOral300 mg
ElixirOral80 mg
LiquidOral80 mg/15mL
TabletOral
TabletOral300 mg/1
SyrupOral
Kit
Capsule, extended releaseOral100 mg
Capsule, extended releaseOral200 mg
Capsule, extended releaseOral300 mg
Capsule, extended releaseOral50 mg
Capsule, extended releaseOral100 mg/1
Capsule, extended releaseOral400 mg/1
Tablet, extended releaseOral450 mg
SolutionOral80 mg
TabletOral125000 ug/1
TabletOral250000 ug/1
Tablet, extended releaseOral250 mg
Tablet, extended releaseOral500 mg
TabletOral125 mg
TabletOral250 mg
Capsule, extended releaseOral125 mg/1
Capsule, extended releaseOral200 mg/1
Capsule, extended releaseOral300 mg/1
SolutionOral80 mg/15mL
Tablet, extended releaseOral100 mg/1
Tablet, extended releaseOral450 mg/1
Tablet, extended releaseOral600 mg/1
Tablet, extended releaseOral200 mg/1
SolutionIntravenous
LiquidOral80 mg
Tablet, extended releaseOral300 mg/1
InjectionIntravenous
Injection, solutionIntravenous
Injection, solutionIntravenous160 mg/100mL
Injection, solutionIntravenous200 mg/100mL
Injection, solutionIntravenous320 mg/100mL
Injection, solutionIntravenous40 mg/100mL
Injection, solutionIntravenous400 mg/100mL
Injection, solutionIntravenous80 mg/100mL
ElixirOral
Tablet, extended releaseOral400 mg/1
TabletOral400 mg/1
TabletOral600 mg/1
Tablet, extended releaseOral400 mg
Tablet, extended releaseOral600 mg
Prices
Unit descriptionCostUnit
Elixophyllin GG 100-100 mg/15ml Solution 240ml Bottle60.98USD bottle
Uniphyl 600 mg 24 Hour tablet2.28USD tablet
Theo-24 400 mg 24 Hour Capsule2.04USD capsule
Theo-24 400 mg capsule sa1.97USD capsule
Uniphyl 400 mg 24 Hour tablet1.58USD tablet
Theo-24 300 mg 24 Hour Capsule1.45USD capsule
Theo-24 300 mg capsule sa1.4USD capsule
Theophylline 400 mg 24 Hour tablet1.27USD tablet
Theo-24 200 mg 24 Hour Capsule1.25USD capsule
Theo-24 200 mg capsule sa1.14USD capsule
Theochron 450 mg tablet sa0.94USD tablet
Theophylline CR 300 mg 12 Hour Capsule0.93USD capsule
Theo-24 100 mg 24 Hour Capsule0.83USD capsule
Theophylline CR 200 mg 12 Hour Capsule0.79USD capsule
Theophylline CR 450 mg 12 Hour tablet0.79USD tablet
Theo-24 100 mg capsule sa0.76USD capsule
Quibron 90-150 mg capsule0.73USD capsule
Theophylline CR 125 mg 12 Hour Capsule0.73USD capsule
Uniphyl 600 mg Sustained-Release Tablet0.68USD tablet
Uniphyl 400 mg Sustained-Release Tablet0.56USD tablet
Theochron 300 mg tablet sa0.54USD tablet
Theophylline CR 300 mg 12 Hour tablet0.51USD tablet
Theophylline CR 200 mg 12 Hour tablet0.4USD tablet
Theochron 200 mg tablet sa0.33USD tablet
Theophylline CR 100 mg 12 Hour tablet0.3USD tablet
Elixophyllin GG 100-100 mg/15ml Solution0.24USD ml
Theochron 100 mg tablet sa0.23USD tablet
Elixophyllin 80 mg/15ml Elixir0.2USD ml
Elixophyllin 80 mg/15 ml elix0.19USD ml
Apo-Theo La 300 mg Sustained-Release Tablet0.15USD tablet
Apo-Theo La 100 mg Sustained-Release Tablet0.14USD tablet
Apo-Theo La 200 mg Sustained-Release Tablet0.14USD tablet
Theophylline anhydrous powder0.08USD g
Theophylline 200 mg/100 ml d5w0.06USD ml
Theolair 5.3 mg/ml Liquid0.03USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)273 °CPhysProp
water solubility7360 mg/L (at 25 °C)YALKOWSKY,SH & HE,Y (2003)
logP-0.02HANSCH,C ET AL. (1995)
Caco2 permeability-4.35ADME Research, USCD
pKa8.81KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility22.9 mg/mLALOGPS
logP-0.26ALOGPS
logP-0.77ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)7.82ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.93 m3·mol-1ChemAxon
Polarizability16.86 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9902
Caco-2 permeable+0.6172
P-glycoprotein substrateNon-substrate0.7281
P-glycoprotein inhibitor INon-inhibitor0.8939
P-glycoprotein inhibitor IINon-inhibitor0.911
Renal organic cation transporterNon-inhibitor0.8807
CYP450 2C9 substrateNon-substrate0.7738
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateNon-substrate0.5974
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9933
CYP450 2D6 inhibitorNon-inhibitor0.9827
CYP450 2C19 inhibitorNon-inhibitor0.9895
CYP450 3A4 inhibitorNon-inhibitor0.9616
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9956
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9447
BiodegradationReady biodegradable0.5942
Rat acute toxicity2.7898 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8819
hERG inhibition (predictor II)Non-inhibitor0.8927
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (2.96 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0f79-6970000000-224461ad62a44dbdf860
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-001j-7900000000-a08735d528e738752429
GC-MS Spectrum - CI-BGC-MSsplash10-001i-0900000000-d0882f7d959c726e7623
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9700000000-8d0e1898a6571fbca10a
GC-MS Spectrum - GC-MSGC-MSsplash10-0f79-6970000000-224461ad62a44dbdf860
Mass Spectrum (Electron Ionization)MSsplash10-00lr-9500000000-2c8464c2fe84464c207f
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-0900000000-0092516012d6a2a93b31
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00di-4900000000-dcf52c18a6996f412b1a
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00kf-9000000000-09089337909892ef44cb
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-001j-7900000000-a08735d528e738752429
MS/MS Spectrum - CI-B (Unknown) , PositiveLC-MS/MSsplash10-001i-0900000000-d0882f7d959c726e7623
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-0900000000-c4943571126a44bb9e5a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004i-0900000000-bc12ce29acd02fa749b8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-03k9-0900000000-d63f60043f186fbb9bc0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-070l-4900000000-d293ab2fa6199dbaf97a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-05ru-9400000000-dde4775588d52c83806f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-0900000000-556e382f583d610ef1f0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004i-0900000000-89e34f5158856ba33469
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-03k9-0900000000-65a6897d72954e875b00
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-070l-4900000000-df16604bd6c40cee8f24
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-05r3-9500000000-39a721dcecc86ed95507
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-001i-1900000000-e67ff7ef9a955b90eb3f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-001i-3900000000-1870952d98dbba22ace8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00di-7900000000-dc0e9606776c43a7823f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-014j-9300000000-2c4c6490dda3ed3b563f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-9000000000-26a6c0c23a465afdcde1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-01q9-1900000000-b11ca3441bb29fef1906
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0002-9400000000-63726fe0b49a9dc6ba7e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00di-9100000000-139f765bc9b5855960c6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-00di-9000000000-88b5cb393b960973ac64
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-00yi-9000000000-1ebbddce3c7133972546
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-f85319d9f010d9331358
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-aa13286b9e614fd8fe53
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-e15e11a3656aeeab5cd9
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03mi-0900000000-2a03f291514704faa75f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03k9-2900000000-ab88f9462f7fd47e2cdb
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-02il-5900000000-10615507746dde65941c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-016r-9300000000-23b6aaf5dc6055695076
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9100000000-0cbbbe667a26bdb5e69c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9000000000-ae6306e2b4613a843262
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-c4943571126a44bb9e5a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-bc12ce29acd02fa749b8
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03k9-0900000000-024b4b169aaa17d8a74e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-070l-4900000000-d293ab2fa6199dbaf97a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-05ru-9400000000-dde4775588d52c83806f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-556e382f583d610ef1f0
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-89e34f5158856ba33469
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03k9-0900000000-65a6897d72954e875b00
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-070l-4900000000-983504ecebbfb75b5084
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-05r3-9500000000-39a721dcecc86ed95507
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-03fr-0900000000-301f6a6c606c9a7b0a70
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-03di-0900000000-605dffad97fe00830afb
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-03di-0900000000-a555f5610ea0cc93fb51
MS/MS Spectrum - , negativeLC-MS/MSsplash10-004i-0900000000-f549c20fef4bb5ca418e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-f1e7ed4d06480c676ae5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0089-0900000000-b98ed10778362fb92f0f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-da2d25abcc877a840ad2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-abde646c11db3466840e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0089-0900000000-dbb621bedc8cfcd20c79
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-2900000000-90c98019c1e8f7da070b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-7900000000-cb3893a87548cb64cf27
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ba-9400000000-0063418efb7894950690
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-9100000000-f981abb3cf2d588f83ed
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-9100000000-f0fbdf55d630257724bf
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0gb9-9000000000-fe69541c14c87da8c124
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-1900000000-e67ff7ef9a955b90eb3f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-3900000000-1870952d98dbba22ace8
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-7900000000-b5c4010c670127e11063
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014j-9300000000-2c4c6490dda3ed3b563f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-26a6c0c23a465afdcde1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01q9-1900000000-c1f0683d1932a6c393f8
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0002-9400000000-63726fe0b49a9dc6ba7e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9100000000-139f765bc9b5855960c6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9000000000-88b5cb393b960973ac64
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00yi-9000000000-a92e0f58a066f6e1c88b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0900000000-08f49d05e8c651dd89ec
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-1900000000-bad7ec3fbdf7e1eecae4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01ba-9500000000-fadd3d94aac67bb5574b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-9200000000-426452757fca6f6b9b76
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-9100000000-52e441104cd15fca9363
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0900000000-d8a03644c7ee59de6416
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0900000000-6016ebc9f342f37971a7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0930000000-7539c4c857812dd013e7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0930000000-17caee7404f50a2538bb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-1900000000-d5c161725a650cbeb97c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-2910000000-c9eb85b2c5aaf500073c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0900000000-08b71a19d1a98ad63f16
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-cc9a16a03fd1ddcf16ce
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Xanthines
Alternative Parents
6-oxopurines / Alkaloids and derivatives / Pyrimidones / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Xanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Pyrimidone / Pyrimidine / Azole / Imidazole / Heteroaromatic compound / Vinylogous amide
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dimethylxanthine (CHEBI:28177) / Purine alkaloids (C07130) / a small molecule (CPD-12479)

Targets

Details
1. Adenosine receptor A1
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Purine nucleoside binding
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
ADORA1
Uniprot ID
P30542
Uniprot Name
Adenosine receptor A1
Molecular Weight
36511.325 Da
References
  1. Nantwi KD, Basura GJ, Goshgarian HG: Adenosine A1 receptor mRNA expression and the effects of systemic theophylline administration on respiratory function 4 months after C2 hemisection. J Spinal Cord Med. 2003 Winter;26(4):364-71. [PubMed:14992338]
  2. Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [PubMed:3588607]
Details
2. Adenosine receptor A2a
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Identical protein binding
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name
ADORA2A
Uniprot ID
P29274
Uniprot Name
Adenosine receptor A2a
Molecular Weight
44706.925 Da
References
  1. Pechlivanova DM, Georgiev VP: Effects of single and long-term theophylline treatment on the threshold of mechanical nociception: contribution of adenosine A1 and alpha2-adrenoceptors. Methods Find Exp Clin Pharmacol. 2005 Nov;27(9):659-64. [PubMed:16357952]
  2. Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [PubMed:3588607]
Details
3. Adenosine receptor A2b
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled adenosine receptor activity
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name
ADORA2B
Uniprot ID
P29275
Uniprot Name
Adenosine receptor A2b
Molecular Weight
36332.655 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Philipp S, Yang XM, Cui L, Davis AM, Downey JM, Cohen MV: Postconditioning protects rabbit hearts through a protein kinase C-adenosine A2b receptor cascade. Cardiovasc Res. 2006 May 1;70(2):308-14. Epub 2006 Feb 23. [PubMed:16545350]
  3. Phelps PT, Anthes JC, Correll CC: Characterization of adenosine receptors in the human bladder carcinoma T24 cell line. Eur J Pharmacol. 2006 Apr 24;536(1-2):28-37. Epub 2006 Mar 3. [PubMed:16581066]
  4. Fozard JR, Baur F, Wolber C: Antagonist pharmacology of adenosine A2B receptors from rat, guinea pig and dog. Eur J Pharmacol. 2003 Aug 15;475(1-3):79-84. [PubMed:12954362]
  5. Holgate ST: The Quintiles Prize Lecture 2004. The identification of the adenosine A2B receptor as a novel therapeutic target in asthma. Br J Pharmacol. 2005 Aug;145(8):1009-15. [PubMed:15980878]
  6. Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [PubMed:3588607]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging f...
Gene Name
PDE4B
Uniprot ID
Q07343
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 4B
Molecular Weight
83342.695 Da
References
  1. Lipworth BJ: Phosphodiesterase-4 inhibitors for asthma and chronic obstructive pulmonary disease. Lancet. 2005 Jan 8-14;365(9454):167-75. [PubMed:15639300]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, ...
Gene Name
PDE5A
Uniprot ID
O76074
Uniprot Name
cGMP-specific 3',5'-cyclic phosphodiesterase
Molecular Weight
99984.14 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name
PDE4A
Uniprot ID
P27815
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 4A
Molecular Weight
98142.155 Da
References
  1. Wang K, Chen JQ, Chen Z, Chen JC: Inhibition of human phosphodiesterase 4A expressed in yeast cell GL62 by theophylline, rolipram, and acetamide-45. Acta Pharmacol Sin. 2002 Nov;23(11):1013-7. [PubMed:12421478]
  2. Haider S: Cyclic AMP level and phosphodiesterase activity during 17alpha,20beta-dihydroxy-4-pregnen-3-one induction and theophylline inhibition of oocyte maturation in the catfish, Clarias batrachus. Comp Biochem Physiol A Mol Integr Physiol. 2003 Feb;134(2):267-74. [PubMed:12547256]
  3. Rickards KJ, Andrews MJ, Waterworth TH, Alexander GB, Cunningham FM: Differential effects of phosphodiesterase inhibitors on platelet activating factor (PAF)- and adenosine diphosphate (ADP)-induced equine platelet aggregation. J Vet Pharmacol Ther. 2003 Aug;26(4):277-82. [PubMed:12887610]
  4. Usta C, Sadan G, Tuncel B: The effect of the indomethacin on phosphodiesterase inhibitors mediated responses in isolated trachea preparations. Prostaglandins Leukot Essent Fatty Acids. 2004 Sep;71(3):137-41. [PubMed:15253881]
  5. Lee JM, Zemans RL, Hejazi M, Chin BB, Ladenson PW, Caturegli P: Modulation of thyroidal radioiodine uptake by theophylline. Exp Mol Pathol. 2004 Oct;77(2):116-20. [PubMed:15351234]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes.
Gene Name
PDE3A
Uniprot ID
Q14432
Uniprot Name
cGMP-inhibited 3',5'-cyclic phosphodiesterase A
Molecular Weight
124978.06 Da
References
  1. Rickards KJ, Andrews MJ, Waterworth TH, Alexander GB, Cunningham FM: Differential effects of phosphodiesterase inhibitors on platelet activating factor (PAF)- and adenosine diphosphate (ADP)-induced equine platelet aggregation. J Vet Pharmacol Ther. 2003 Aug;26(4):277-82. [PubMed:12887610]
  2. Wu BN, Lin RJ, Lo YC, Shen KP, Wang CC, Lin YT, Chen IJ: KMUP-1, a xanthine derivative, induces relaxation of guinea-pig isolated trachea: the role of the epithelium, cyclic nucleotides and K+ channels. Br J Pharmacol. 2004 Aug;142(7):1105-14. Epub 2004 Jul 5. [PubMed:15237094]
  3. Kajikawa S, Kigami D, Nakayama H, Doi K: Changes in submaxillary gland gene expression in F344 rats by multiple dosing of theophylline. Exp Anim. 2006 Apr;55(2):143-6. [PubMed:16651698]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Activator
General Function
Transcription factor binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
Gene Name
HDAC2
Uniprot ID
Q92769
Uniprot Name
Histone deacetylase 2
Molecular Weight
55363.855 Da
References
  1. Ito K, Lim S, Caramori G, Cosio B, Chung KF, Adcock IM, Barnes PJ: A molecular mechanism of action of theophylline: Induction of histone deacetylase activity to decrease inflammatory gene expression. Proc Natl Acad Sci U S A. 2002 Jun 25;99(13):8921-6. Epub 2002 Jun 17. [PubMed:12070353]
  2. Cosio BG, Tsaprouni L, Ito K, Jazrawi E, Adcock IM, Barnes PJ: Theophylline restores histone deacetylase activity and steroid responses in COPD macrophages. J Exp Med. 2004 Sep 6;200(5):689-95. Epub 2004 Aug 30. [PubMed:15337792]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Calcium-dependent phospholipid-binding protein that plays a role in calcium-mediated intracellular processes (PubMed:14674885). Involved in the TNF-alpha receptor signaling pathway in a calcium-dependent manner (PubMed:14674885). Exhibits calcium-dependent phospholipid binding properties (PubMed:9430674, PubMed:19539605). Plays a role in neuronal progenitor cell differentiation; induces neurite outgrowth via a AKT-dependent signaling cascade and calcium-independent manner (PubMed:23263657, PubMed:25450385). May recruit target proteins to the cell membrane in a calcium-dependent manner (PubMed:12522145). May function in membrane trafficking (PubMed:9430674). Involved in TNF-alpha-induced NF-kappa-B transcriptional repression by inducing endoprotease processing of the transcription factor NF-kappa-B p65/RELA subunit (PubMed:18212740). Also induces endoprotease processing of NF-kappa-B p50/NFKB1, p52/NFKB2, RELB and REL (PubMed:18212740).
Specific Function
Calcium ion binding
Gene Name
CPNE1
Uniprot ID
Q99829
Uniprot Name
Copine-1
Molecular Weight
59058.34 Da
References
  1. Marwick JA, Wallis G, Meja K, Kuster B, Bouwmeester T, Chakravarty P, Fletcher D, Whittaker PA, Barnes PJ, Ito K, Adcock IM, Kirkham PA: Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802. doi: 10.1016/j.bbrc.2008.10.065. Epub 2008 Oct 23. [PubMed:18951874]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Catalyzes intramembrane proteolysis of some signal peptides after they have been cleaved from a preprotein, resulting in the release of the fragment from the ER membrane into the cytoplasm. Required to generate lymphocyte cell surface (HLA-E) epitopes derived from MHC class I signal peptides (PubMed:11714810). May be necessary for the removal of the signal peptide that remains attached to the hepatitis C virus core protein after the initial proteolytic processing of the polyprotein (PubMed:12145199). Involved in the intramembrane cleavage of the integral membrane protein PSEN1 (PubMed:12077416, PubMed:11714810, PubMed:14741365). Cleaves the integral membrane protein XBP1 isoform 1 in a DERL1/RNF139-dependent manner (PubMed:25239945). May play a role in graft rejection (By similarity).
Specific Function
Aspartic endopeptidase activity, intramembrane cleaving
Gene Name
HM13
Uniprot ID
Q8TCT9
Uniprot Name
Minor histocompatibility antigen H13
Molecular Weight
41487.86 Da
References
  1. Marwick JA, Wallis G, Meja K, Kuster B, Bouwmeester T, Chakravarty P, Fletcher D, Whittaker PA, Barnes PJ, Ito K, Adcock IM, Kirkham PA: Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802. doi: 10.1016/j.bbrc.2008.10.065. Epub 2008 Oct 23. [PubMed:18951874]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
May antagonize Nodal signaling.
Specific Function
Carbohydrate binding
Gene Name
NOMO1
Uniprot ID
Q15155
Uniprot Name
Nodal modulator 1
Molecular Weight
134323.005 Da
References
  1. Marwick JA, Wallis G, Meja K, Kuster B, Bouwmeester T, Chakravarty P, Fletcher D, Whittaker PA, Barnes PJ, Ito K, Adcock IM, Kirkham PA: Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802. doi: 10.1016/j.bbrc.2008.10.065. Epub 2008 Oct 23. [PubMed:18951874]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Involved in the base excision repair (BER) pathway, by catalyzing the poly(ADP-ribosyl)ation of a limited number of acceptor proteins involved in chromatin architecture and in DNA metabolism. This ...
Gene Name
PARP1
Uniprot ID
P09874
Uniprot Name
Poly [ADP-ribose] polymerase 1
Molecular Weight
113082.945 Da
References
  1. Marwick JA, Wallis G, Meja K, Kuster B, Bouwmeester T, Chakravarty P, Fletcher D, Whittaker PA, Barnes PJ, Ito K, Adcock IM, Kirkham PA: Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802. doi: 10.1016/j.bbrc.2008.10.065. Epub 2008 Oct 23. [PubMed:18951874]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Promotes functional expression of homomeric alpha-7 and alpha-8 nicotinic acetylcholine receptors at the cell surface. May also promote functional expression of homomeric serotoninergic 5-HT3 receptors, and of heteromeric acetylcholine receptors alpha-3/beta-2, alpha-3/beta-4, alpha-4/beta-2 and alpha-4/beta-4.
Specific Function
Acetylcholine receptor binding
Gene Name
RIC3
Uniprot ID
Q7Z5B4
Uniprot Name
Protein RIC-3
Molecular Weight
41091.77 Da
References
  1. Marwick JA, Wallis G, Meja K, Kuster B, Bouwmeester T, Chakravarty P, Fletcher D, Whittaker PA, Barnes PJ, Ito K, Adcock IM, Kirkham PA: Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802. doi: 10.1016/j.bbrc.2008.10.065. Epub 2008 Oct 23. [PubMed:18951874]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Monoglycylase which modifies alpha- and beta-tubulin, generating side chains of glycine on the gamma-carboxyl groups of specific glutamate residues within the C-terminal tail of alpha- and beta-tubulin. Involved in the side-chain initiation step of the glycylation reaction by adding a single glycine chain to generate monoglycine side chains. Not involved in elongation step of the polyglycylation reaction.
Specific Function
Atp binding
Gene Name
TTLL3
Uniprot ID
Q9Y4R7
Uniprot Name
Tubulin monoglycylase TTLL3
Molecular Weight
87413.395 Da
References
  1. Marwick JA, Wallis G, Meja K, Kuster B, Bouwmeester T, Chakravarty P, Fletcher D, Whittaker PA, Barnes PJ, Ito K, Adcock IM, Kirkham PA: Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802. doi: 10.1016/j.bbrc.2008.10.065. Epub 2008 Oct 23. [PubMed:18951874]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Brosen K: Drug interactions and the cytochrome P450 system. The role of cytochrome P450 1A2. Clin Pharmacokinet. 1995;29 Suppl 1:20-5. [PubMed:8846619]
  2. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  4. Sarkar MA, Hunt C, Guzelian PS, Karnes HT: Characterization of human liver cytochromes P-450 involved in theophylline metabolism. Drug Metab Dispos. 1992 Jan-Feb;20(1):31-7. [PubMed:1346993]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  6. Theophylline FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Zinc ion binding
Specific Function
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, an...
Gene Name
ADA
Uniprot ID
P00813
Uniprot Name
Adenosine deaminase
Molecular Weight
40764.13 Da
References
  1. Saboury AA, Bagheri S, Ataie G, Amanlou M, Moosavi-Movahedi AA, Hakimelahi GH, Cristalli G, Namaki S: Binding properties of adenosine deaminase interacted with theophylline. Chem Pharm Bull (Tokyo). 2004 Oct;52(10):1179-82. [PubMed:15467230]
  2. Singh LS, Sharma R: Purification and characterization of intestinal adenosine deaminase from mice. Mol Cell Biochem. 2000 Jan;204(1-2):127-34. [PubMed:10718633]
  3. Bandyopadhyay BC, Poddar MK: Theophylline-induced changes in mammalian adenosine deaminase activity and corticosterone status: possible relation to immune response. Methods Find Exp Clin Pharmacol. 1997 Apr;19(3):181-4. [PubMed:9203166]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Sarkar MA, Hunt C, Guzelian PS, Karnes HT: Characterization of human liver cytochromes P-450 involved in theophylline metabolism. Drug Metab Dispos. 1992 Jan-Feb;20(1):31-7. [PubMed:1346993]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Ha HR, Chen J, Freiburghaus AU, Follath F: Metabolism of theophylline by cDNA-expressed human cytochromes P-450. Br J Clin Pharmacol. 1995 Mar;39(3):321-6. [PubMed:7619675]
  3. Zhang ZY, Kaminsky LS: Characterization of human cytochromes P450 involved in theophylline 8-hydroxylation. Biochem Pharmacol. 1995 Jul 17;50(2):205-11. [PubMed:7632164]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
References
  1. Kobayashi Y, Sakai R, Ohshiro N, Ohbayashi M, Kohyama N, Yamamoto T: Possible involvement of organic anion transporter 2 on the interaction of theophylline with erythromycin in the human liver. Drug Metab Dispos. 2005 May;33(5):619-22. Epub 2005 Feb 11. [PubMed:15708966]

Drug created on June 13, 2005 07:24 / Updated on November 20, 2018 13:19